I Could Have Loved You
by DWScribe
Summary: An AU story that I've started. ••• It all started with a fight between Dean and his brother, it sets of a chain of events that Dean doesn't know how to get himself out of. During the chaos, he reconnects with someone from his past. It brings back a lot of memories and soon enough Dean is standing face to face with a lot of decisions. Can he still hunt without his brother?
1. Chapter One: Packing Up

**Disclaimer:** I don't own Supernatural or its characters. I actually uploaded this Fanfiction on Wattpad first, but thought I'd try this platform out as well. Feedback would be great! I hope you guys like it. I know this first chapter is short, but the others are longer!

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 **Chapter One: Packing Up**

Dean expelled a sigh, their case was _finally_ over! Where there was usually genuine relief and maybe even cause for a small celebration, Winchester style, this wasn't one of those times. Dean knew they'd been lucky to get out of it alive, and to make matters even worse, they'd lost someone along the way. Staying put in the same town for a while, for a case, was usually a quite welcome change. The downside to have a case stretch out over a couple of weeks was, however, that you got to know people. You got close to people with whom you'd never had a relationship with otherwise. Be it local law enforcement, witnesses, families, or people that came to relate to the case as it progressed. Dean was cradling a six pack of beer in his arms, along with two brown paper bags, he felt a million times lighter today than he had the day before. "What a difference a day makes, huh?" He chuckled to himself. He managed to knock on the door with his elbow.

"Lemme in," he called towards the door. He could hear Sammy shuffling around in there. "I've got food," he added.

Within seconds his younger brother Sam opened the door, but quickly turned around and continued with his packing. Dean couldn't exactly blame him, they'd been stuck in this motel room for so long, and he was itching to get back on the road too, but not until he had some food in him, he was starving. He started unloading the content of the brown paper bags onto the table: the two hamburgers, the carton of fries, and the condiments. When he was done he grabbed one of the beer cans and opened it up, it was still a bit cold; just the way he liked it. "Mm," a sigh of content came from the hunter's lips as he took a greedy sip of the beer.

"Y'wanna eat?" He glanced over at his brother who was still busy packing.

Just watching him made Dean shake his head, Sam was such a neat freak. He always insisted on folding everything carefully into his duffel bag, even when it'd end up getting tossed around in the trunk of the car anyway. When Sam didn't respond, he just shrugged and started folding away the paper around one of the burgers before he took a big bite. "Now this is..." he said in appreciative tone, still chewing.

"Hey, Sammy, c'mon. The sooner we eat; the sooner we can get the hell outta here."

Eventually Sam stopped packing and sauntered over to the table, still without saying a word. Dean groaned, his brother was obviously in a mood and even if he knew what had contributed to it, it made him feel uncomfortable. This wasn't how Sam usually were, then again, their cases rarely ended this way.

"Hey man, I know that—"

"Dean, I really don't wanna talk about it, okay?"

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 **I hope you all liked it, please comment!**


	2. Chapter Two: The Fight

**A/N:** If you want to, listen to 'The Sound of Silence - Disturbed' for effect.

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 **Chapter Two: The Fight**

They continued to eat in silence and Dean did his best to ignore the urge to talk to his brother about what had happened. He was just about to say something, when his cellphone broke the silence. With furrowed brows as he managed to fish it out of his pocket. For Dean Winchester, the calls that came through on this phone were rarely, if ever, of a positive nature.

"It's Jody," he announced as he saw the caller-ID. Of course, the display didn't show her actual name, if he ever lost the phone, even if Charlie had added some encryption to it to make it difficult to crack; he couldn't be too careful. He rose to his feet and started walking around the room as he listened to Jody telling him about something she'd stumbled on that she thought might be of the Supernatural variety. Normally, Dean would be happy to get on the road and onward to the next case, but he actually felt drained after this one. Of course, this was his job, and he'd never slack off just because he felt like he needed to. During the phone call he shot glances at his brother who'd now cleared the paper wraps and cartons off the table, and when he sat back down, Dean knew that whatever was up with Sam, wasn't good. This was to be expected considering what had happened during the case, but maybe it was worse than Dean had initially thought. He quickly finished up with Jody and promised that they'd get there as soon as possible.

"People are acting strange, personality changes. Might be possessions," Dean explained, giving a crude analysis as he sat back down at the table. Sam remained quiet for a while.

"Dean..." he started.

A heavy sigh was expelled from the older brother's lips as he heard Sam's tone of voice, he knew he wasn't going to like this.

"I can't do this anymore," Sam continued. "I need to get out."

Dean's emerald green eyes widened considerably as he stared blankly at his brother as his words sank in. "What d'you mean 'you need to get out'?" He spat out in a quite accusatory tone.

Now it was Sam's turn to sigh. "Dean. Come on! We both know that this was supposed to have been a temporary thing. I was happy to come with you 12 years ago, when you picked me up from Stanford—"

"Happy?" Dean rolled his eyes, his tone sarcastic.

"Well, regardless. I'm not saying that you forced me to do any of this, but I'm calling it now. I can't do this anymore, I'm...sorry."

The 'I'm sorry' part didn't sound very convincing, which only fueled Dean's irritation and anger that had started to rise within him.

"You're _sorry?!_ " His tone was raise and the words were dripping with contempt. "What the hell Sammy," he groaned. "I know this case was tough and I'm honestly sorry for what you went through...but things like this happen, you and I both know that, right? Which is _exactly_ why we need to keep doin' this! If we jus' stop, then all the deaths have been for nothin'. I get how you might wanna give up right now, but don't you think I feel like givin' up at times too? Of course I do, but Sammy, c'mon!" He tried his best to reason with his brother and it almost sounded like a plea.

Sam just shook his head in response. "I'm not doing this to upset you Dean, but I'm also not asking for your permission. I'm not denying that we've done good, we have. But it's just time."

"Bullshit!" He yelled. His knuckles paled as he gripped the half-empty beer bottle in his hand, a little harder and he might have actually crushed it. "We need to stick together, isn't that the conclusion we've always reached?" Dean spoke through gritted teeth.

"It was always my plan to go back, to have a normal life, Dean." Sam continued as though he hadn't heard his brother's outburst. "I think I just lost sight of that. My wish was never to be a hunter, I wanted to be a lawyer."

He slammed his fist into the table, hard. His eyes were wild. "You think this was my _wish?!_ " Dean's voice was shaking by now. "You think I had a choice? You think I had the luxury to ever say no? You think dad ever cared about when I felt queasy after seeing chopped off vamp heads?"

Sam's gaze dropped to the floor as their dad was brought into the conversation. "At least he brought you with him," he muttered under his breath.

"Don't give me that Sammy! You always went on about bein' neglected, but you should've been happy about that. I mean, you wanna leave now, what d'you think you would've wanted back then, huh?"

"Mm, you're probably right," Sam mumbled back, sounding tired, defeated even. "I know you never had a choice and I'm sorry about that. I can't change what dad did though. I, however, have a choice right now and I can't keep doing this, Dean. I can't keep watching people I care about die."

Hearing Sam admit to that last part temporarily made him a little bit calmer. Of course, this whole thing, the fight, it was still about this particular case. That was all it was, Dean tried to convince himself. If he was going to have any chance at all to make Sam stay, he needed to stop tip-toeing around what had happened.

"Hey. I don't want that either, y'know that, right? And Liv never should've died."

There it was, it was out there now. Her name seemed to hang in the air between them and he heard a small gasp coming from his brother as her name had been uttered.

"Don't!" Sam exploded. The rapid movement of him getting to his feet caused the chair he'd been sitting on to topple over. "Fuck you, Dean!" He cursed.

Dean was baffled. Sam rarely cursed and he couldn't help a tiny smirk tugging at the corner of his lips. Cursing was usually his area, but when he saw the hurt in his brother's eyes the smirk quickly faded.

"Sam, I'm—"

"Don't you dare say sorry, Dean! I could've saved her; I know I could've!" Sam argued, his voice broke at the end and Dean thought he saw tears well up in his brother's eyes.

"You don't know that, Sammy. All I know is that _you_ could've died if I hadn't helped you outta there."

"Helped?!" Sam yelled.

Before Dean could react, Sam had taken a quick stride across the room and soon the older hunter found himself pinned to the wall by his baby brother.

"You didn't help me. Don't, even for a second, think that you _helped_ me. Your decision killed her. You. Killed. Her."

Sam gave him a last push up against the wall before he released him and quickly turned around to grab his packed duffel bag and jacket. Without so much as another word, Sam charged through the door and slammed it shut behind him. The sound kept echoing in Dean's ears for a few seconds before he realized what had just happened.

Sam was gone, and for the first time ever, Dean felt that there was a real possibility of his brother never coming back.

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 **Reviews are always appreciated, thank you!**


	3. Chapter Three: Alcohol

**Chapter Three: Alcohol**

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Dean sank down in one of the chairs, his body seemed to sag, he felt drained. It felt as though someone had just knocked all the air out of him. Emerald green eyes scanned the room, Sam was gone and even if they both traveled lightly the small motel room seemed a lot emptier now that his brother wasn't there. Briefly, he wondered how Sam was even planning on getting out of the small town, since he was the one with the car. He didn't really have the energy to care though, not right now. As the realization of what had just happened sank in, he felt the irritation starting to build up inside of him again. He reached out for the opened beer bottle on the table and took a swig, but not even the beer tasted good. This only fueled his irritation, of course it was less about the slightly stale beer and more about his brother; Dean just wouldn't admit it. He slammed the bottle down hard.

"Damn you, Sammy," he growled under his breath. "We're supposed to stick together."

He rose to his feet, the force of the movement causing the chair to topple over. There was no point of him staying put, their case was over. Angrily, he started throwing his belongings into his duffel bag and soon headed towards the checkout station. It wasn't until he laid his eyes on the Impala that he felt calmer, his beautiful Baby. He settled in behind the wheel and reached over to turn the radio on. Rock music quickly filled the car as Dean pulled out of the parking lot. He was finally back on the road, this was about the only place where Dean felt safe, and at home. For many years Baby had been the _only_ home, flitting between motel rooms—while he'd gotten used to it—had never felt like home. Of course, lately the Bunker had felt more and more like a home, not just for him, but a home that he could share with his brother; it was almost normal. He figured Sam would be headed towards the Bunker, so at least he knew where he _wasn't_ going.

He drove for hours, but not even putting miles behind him seemed to ease the irritation and the anger he was feeling. It was already dark outside when he finally stopped outside a bar, this was what he needed. There didn't seem to be a motel around, but he could always sleep in the car, after all this wasn't his first rodeo. As he walked up towards the entrance, rock music spilled out into the night and Dean's lips curved up into a smile. This definitely seemed like his type of place. Surprisingly enough the bar was quite busy, even though its location was literally in the middle of nowhere. The hunter observed the crowd and concluded that most of them were nomads like him, people who lived on the road, even if they weren't hunters these were his people. He made it over to the bar and settled down at the counter, he was in the mood to be by himself, if he grabbed a booth he ran the risk of someone coming over; not that these people seemed to be venturing out of their respective groups.

"Can I get a Whiskey neat?" he asked the bartender who nodded in response.

Dean got himself seated and waited for the drink to appear in front of him. The second the amber-colored liquid hit his throat, he could feel himself relax. _This_ was exactly what he needed. He checked his phone quickly, but no missed calls or text messages. Stubbornness was definitely something that ran in the family and Dean didn't exactly expect to hear from Sam anytime soon. Which also meant that he wasn't about to text or call Sam either. Dean quickly stashed his phone away in his jacket pocket before he turned his attention back to his drink. Luckily enough, no one did approach him. At least not until he'd calmed down considerably and on the verge of being tispy, which for Dean Winchester took quite the amount of alcohol.

"You mind if I take a seat? There aren't that many single seats left."

Dean turned his head up as he heard her voice, something about it made him quite sure that she was beautiful before he'd even laid eyes on her. It turned out that he was right. Her hair was a dark brown, its soft curls cascading down her back. She dressed in a way that most girls didn't, but in a way that Dean appreciated very much.

"Course not," he offered with a nod. "Metallica fan, huh?" He grinned as he nodded towards her shirt.

It was a faded, vintage-type looking shirt with cut off sleeves, allowing Dean to see the black lacy fabric of her bra as she reached for the drink she'd ordered.

"Yeah, love 'em," she replied, not exactly inviting him to a conversation. Maybe she wanted to be left alone.

"You've got good taste," he offered before he turned his attention back to his own drink. By now the hunter had lost track of how many he'd had.

Maybe it was because he'd actually shown her that he respected her enough not to be intrusive, but eventually she broke the silence between them.

"So, you a metal fan too?" Her voice sounded casual, but not bored, maybe she was genuinely intrigued by him. He wasn't going to read too much into it though.

"Yeah, well classic rock and metal," he clarified. "But I'm not really into death metal and stuff," he added.

She raised her glass with its clear liquid, "I see you've got good taste too," she winked as she used the line he'd just used.

A small chuckle fell from Dean's lips. "Not to sound too cliche, but what brings you here?" He asked, not wanting their conversation to falter. While he'd previously wanted to be alone, right now he wanted nothing more than to keep her talking. He needed to focus on something else and it gave him something else to do than drink more, something he knew he'd regret it in the morning if he did. Even if he had quite the tolerance that had been built up over the years, he wasn't 25 anymore and unfortunately hangovers weren't that easy to shake nowadays.

The brunette smiled and Dean thought that it suited her. He liked the way she had her bangs cut, it gave her overall edginess a softness.

"I'm just driving through; I'm headed to see some family..." Her voice trailed off as if heading to see her family wasn't a joyous occasion.

"Hey, I get it," he offered. "Family ain't easy," he mumbled.

She raised her eyebrows and for a second Dean was afraid he'd misinterpreted the situation, but then she nodded.

"You got that right," she said while she got the attention of the bartender and ordered herself another drink. Vodka with a twist. "What about you, were are you headed?"

Dean shrugged, it seemed weird to tell the truth, that he had no idea. Surely she'd think that he was hiding something if that's what he'd go with. Instead he went with a simpler version of the truth, "I'm sorta tryin' to escape some family drama."

"I'm sorry to hear that. You wanna talk about it?"

The way she said it, so casually, made it sound quite inviting. But Dean Winchester never vented, or opened up to anyone besides his brother, and even that was quite rare. "That's okay, thanks though. Y'wanna talk 'bout your stuff?" He offered.

"No, I'd rather not think about it, but thanks." She smiled that smile again.

Dean's anger had definitely dissipated by now and he couldn't help but wonder if he had a chance with her. His head was spinning slightly, but it was a comfortable and welcome buzz. "What's your name?"

"Dylan." Before Dean had a chance to say anything else, she quickly added, "I know, I know, it's quite an odd name for a chick."

It somehow made him sad that she was used to people thinking it was weird. "I like it," he said matter-of-factly. "It's cool! I'm Dean," he said, surprised that he'd used his own name. Normally, he'd use one of his cover names.

"It's nice to meet you, Dean."

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 **A/N: Would still love some feedback on this! Hoping you're liking it, anyway.**


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